Highlights from #imakealiving PDX and Looking Ahead to Austin, TX!

FreshBooks is on the road! Last month, we hosted #imakealiving in Portland, Oregon. Next up: Austin, Texas!

With great risk comes great reward—and for small business owners everywhere, this couldn’t ring truer! Plenty of heart, soul and labor goes into the creation and day-to-day of a small business. And guess what? FreshBooks is here for you every step of that journey. Last month, we hosted another #imakealiving event in PDX, otherwise known as Portland, OR. Here’s how it all went down!

Highlights from #imakealiving PDX

Our wonderful panel included Aaron Draplin (Founder of Draplin Design Co.), Courtenay Hameister (author, columnist, copywriter, screenwriter and teacher), Jack Phan (entrepreneur and leadership influencer), Nathalie Weinstein (Co-Owner of PDXpipeline.com). The panelists were introduced by FreshBooks’ Events Manager Paco Arizmendi and the event was moderated by Events & Community Manager Irene Elliott.


#imakealiving was hosted in The Evergreen, a stunning event space in the heart of Portland. Over 100 local freelancers and business owners attended the event where panelists spoke candidly about the road to becoming their own boss—and they didn’t disappoint!

“It wasn’t able making a business; I wanted to make something I like,” says Aaron, who founded the famous Fieldnotes. “In Portland, if you want to make a band, you get your buddies and make a band. But I was seeing that with shoes, clothing, backpacks, so I made a little brand—that’s it.”

Courtenay chimed in and talked about the challenges with imposter syndrome.

“The majority of people I’ve ever talked to have it. I think freelancers have it quite a bit—just this feeling that someone’s going to find you out,” she explains. “I’m a writer, but I wasn’t trained as a writer. When I wrote my book, during my second draft, I simply couldn’t write because in my head were all of these MFAs that I was competing with. I had to figure out a way to get out of that. Part of imposter syndrome is the fear of mediocrity.”


On the discipline of being your own boss, Jack shares his experience. “If you’re working for yourself, it’s easy to get distracted,” he says. “For me, the discipline comes from the fact that if I build a company and bring in clients, they rely on what I bring to them. I need to make sure I complete what I do.”

To close off the discussion, the panelists offered their advice to the audience.

“One of the things you’re going to have to do is sell yourself and a lot of people have trouble with that. Figure out what the benefit of your product is and its unique selling proposition,” Courtenay explains.

Looking Ahead to #imakealiving Austin, TX

For the 5th city on our #imakealiving tour, we’ll be hitting Austin, TX. Each and every #imakealiving event helps to facilitate and inspire connections between small business owners—and we’re honored to be a part of it all. This month, we’re coming with a theme: Creating Your Brand: How You Can Stand Out by Being You. Ready to get the conversation going, Austin? We can’t wait to meet you!

Event: #imakealiving powered by FreshBooks
When: Wednesday, July 25th, 6:30PM–10:00PM PDT
Where: Gather Monroe St. (411 W Monroe, Austin TX)
Details: #imakealiving will host a diverse panel of people from different industries. They’ll share stories about their livelihoods and non-traditional career journeys. Our panelists will then show you how to harness that inspiration and apply it to your own career. Our goal is to motivate and empower you to break out of your comfort zone and take some chances with your career and marketing!
Cost: Free – seeing you thrive is all the payment we need!
Panelists Include: Ebony Stewart, Lucas Aoki, Meshell Baker and Chelsea Francis

about the author

FreshBooks is the #1 accounting software in the cloud designed to make billing painless for small businesses and their teams. Today, over 10 million small businesses use FreshBooks to effortlessly send professional looking invoices, organize expenses and track their billable time.

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